EP3645157B1 - Procédé de préparation d'une barbotine de microcapsules - Google Patents

Procédé de préparation d'une barbotine de microcapsules Download PDF

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Publication number
EP3645157B1
EP3645157B1 EP18732389.4A EP18732389A EP3645157B1 EP 3645157 B1 EP3645157 B1 EP 3645157B1 EP 18732389 A EP18732389 A EP 18732389A EP 3645157 B1 EP3645157 B1 EP 3645157B1
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EP
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Prior art keywords
phase
consumer product
microcapsules
dispersing phase
slurry
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EP18732389.4A
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German (de)
English (en)
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EP3645157A1 (fr
Inventor
Lahoussine Ouali
Marlene Jacquemond
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Firmenich SA
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Firmenich SA
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/14—Polymerisation; cross-linking
    • B01J13/16—Interfacial polymerisation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/85—Polyesters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/87—Polyurethanes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/88—Polyamides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/20—After-treatment of capsule walls, e.g. hardening
    • B01J13/22—Coating
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/06—Powder; Flakes; Free-flowing mixtures; Sheets
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3707—Polyethers, e.g. polyalkyleneoxides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3715—Polyesters or polycarbonates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/373—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicones
    • C11D3/3738—Alkoxylated silicones
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/505—Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/805—Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/20—After-treatment of capsule walls, e.g. hardening

Definitions

  • the present invention relates to a process for preparing a microcapsule slurry. More particularly, the process of the invention is characterized by the fact that it requires limited amounts of water for preparing microcapsules.
  • a core-shell microcapsule slurry obtainable by said process as well as consumer products comprising said slurry are also objects of the invention.
  • Perfumes are widely used in consumer products such as detergents, softeners, shower gel, shampoo and play a very important role in those products since they often drive the consumer's choice for a given product.
  • the performance in terms of stability represents an important requirement for perfume delivery systems.
  • these delivery systems also must exhibit good performance in terms of perfume release, either during the wash / lathering phase (blooming) or on dry substrate (skin, hair, textile or home surface) after the wash.
  • microcapsules obtained via interfacial polymerization are widely used.
  • an oil-in-water emulsion or a water-in-oil emulsion is prepared with monomers or polymers soluble in oil phase (such as polyisocyanates) and with polymers soluble in water phase (such as polyamine, polyol).
  • monomers or polymers soluble in oil phase such as polyisocyanates
  • polymers soluble in water phase such as polyamine, polyol
  • the nature of the shell therefore depends on the nature of the momomers or polymers present respectively in the oil phase and in the water phase.
  • a polyurea shell is obtained when a polyisocyanate reacts with a polyamine whereas a polyurethane shell is obtained when a polyisocyanate reacts with a polyol.
  • Processes for producing such microcapsules are widely disclosed in the prior art. Examples of processes for the preparation of polyurea- and polyureathane-based microcapsule slurries are for instance described in WO2007/004166 , EP 2300146 or yet EP2579976 . US 2016/346753 A1 discloses a process to prepare microcapsules.
  • the present invention satisfies this and other needs of the industry.
  • microcapsules encapsulating a hydrophobic active ingredient such as a perfume oil could be obtained by forming a wall formed from the polymerisation of a monomer present in the oil phase with optionally a reactant in the presence of very limited amounts of water or even no water added during the process.
  • a first object of the invention is therefore a process for preparing a microcapsule slurry, said process comprising the steps of:
  • a second object of the invention is a microcapsule slurry obtainable by the process described above, wherein the slurry comprises below or equal to 10%, preferably below or equal to 5%, more preferably below or equal to 3% by weight of water based on the total weight of the slurry and wherein the dispersing phase is hydrophilic.
  • a third and fourth objects of the invention are respectively a perfuming composition and consumer products comprising said microcapsule slurry, as defined in the claims.
  • % is meant to designate percentages by weight of a composition.
  • a “microcapsule”, or the similar, in the present invention is meant to designate a capsule having a core-shell structure and that has a particle size distribution in the micron range (e.g. a mean diameter (d(v, 0.5)) comprised between about 1 and 3000 ⁇ m) and comprises an external solid oligomer-based shell or a polymeric shell and an internal phase enclosed by the external shell.
  • a mean diameter d(v, 0.5)
  • monomer it is meant a molecule that, as unit, reacts or binds chemically to form a polymer or supramolecular polymer. According to an embodiment, the monomer reacts during the interfacial polymerization to form microcapsules in the form of a slurry. Microcapsules may result from the reaction between the monomer and a reactant or may result only from the autopolymerization of the monomer.
  • polyurea-based wall or shell it is meant that the polymer comprises urea linkages produced by either an amino-functional crosslinker or hydrolysis of isocyanate groups to produce amino groups capable of further reacting with isocyanate groups during interfacial polymerization.
  • polyurethane-based wall or shell it is meant that the polymer comprises urethane linkages produced by reaction of a polyol with the isocyanate groups during interfacial polymerization.
  • dispersion in the present invention it is meant a system in which particles are dispersed in a continuous phase of a different composition and it specifically includes a suspension or an emulsion.
  • hydrophobic active ingredient any active ingredient - single ingredient or a mixture of ingredients - which forms a two-phases dispersion when mixed with water.
  • Hydrophobic active ingredients are preferably chosen from the group consisting of flavor, flavor ingredients, perfume, perfume ingredients, nutraceuticals, cosmetics, insect control agents, biocide actives and mixtures thereof.
  • insect control agents present in the hydrophobic internal phase do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of its general knowledge and according to the intended use or application.
  • insect control agents are birch, DEET (N,N-diethyl-m-toluamide), essential oil of the lemon eucalyptus (Corymbia citriodora) and its active compound p-menthane-3,8-diol(PMD), icaridin (hydroxyethyl isobutyl piperidine carboxylate), Nepelactone, Citronella oil, Neem oil, Bog Myrtle (Myrica Gale), Dimethyl carbate, Tricyclodecenyl allyl ether, IR3535 (3-[N-Butyl-N-acetyl]-aminopropionic acid, ethyl ester, Ethylhcxancdiol, Dimethyl phthalate, Metofluthrin, Indalonc, SS220, anthranilate-based insect repellents, and mixtures thereof.
  • DEET N,N-diethyl-m-toluamide
  • the hydrophobic-active ingredient comprises a mixture of a perfume with another ingredient selected from the group consisting of nutraceuticals, cosmetics, insect control agents and biocide actives.
  • the hydrophobic active ingredient comprises a perfume.
  • the hydrophobic active ingredient consists of a perfume.
  • perfume oil (or also “perfume”) what is meant here is an ingredient of composition that is a liquid at about 20°C.
  • said perfume oil can be a perfuming ingredient alone or a mixture of ingredients in the form of a perfuming composition.
  • a perfuming ingredient it is meant here a compound, which is used for the primary purpose of conferring or modulating an odor.
  • such an ingredient, to be considered as being a perfuming one must be recognized by a person skilled in the art as being able to at least impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor.
  • perfume oil also includes combination of perfuming ingredients with substances which together improve, enhance or modify the delivery of the perfuming ingredients, such as perfume precursors, emulsions or dispersions, as well as combinations which impart an additional benefit beyond that of modifying or imparting an odor, such as long-lasting, blooming, malodor counteraction, antimicrobial effect, microbial stability, insect control.
  • perfuming ingredients such as perfume precursors, emulsions or dispersions, as well as combinations which impart an additional benefit beyond that of modifying or imparting an odor, such as long-lasting, blooming, malodor counteraction, antimicrobial effect, microbial stability, insect control.
  • perfuming ingredients present in the hydrophobic internal phase do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of its general knowledge and according to intended use or application and the desired organoleptic effect.
  • these perfuming ingredients belong to chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin. Many of these co-ingredients are in any case listed in reference texts such as the book by S.
  • the perfuming ingredients may be dissolved in a solvent of current use in the perfume industry.
  • the solvent is preferably not an alcohol.
  • solvents are diethyl phthalate, isopropyl myristate, Abalyn ® (rosin resins, available from Eastman), benzyl benzoate, ethyl citrate, limonene or other terpenes, or isoparaffins.
  • the solvent is very hydrophobic and highly sterically hindered, like for example Abalyn ® or benzyl benzoate.
  • the perfume comprises less than 30% of solvent. More preferably the perfume comprises less than 20% and even more preferably less than 10% of solvent, all these percentages being defined by weight relative to the total weight of the perfume. Most preferably, the perfume is essentially free of solvent.
  • a first object of the invention is a process for preparing a microcapsule slurry, said process comprising the steps of:
  • the Applicant is of the opinion that the dispersing phase having a limited amount of water allows a better control of the reactions kinetic during the interfacial polymerisation resulting in high quality membrane formation.
  • the microcapsule slurry obtained/obtainable by the process of the invention can be used not only in aqueous consumer product (since the dispersing phase is highly miscible with water) but also in anhydrous consumer product (without any drying step).
  • microcapsules obtained by the process of the present invention do not need to be dried when incorporated in anhydrous consumer product leading to a cost-effective process.
  • the shell prepared by the process of the invention depends notably on the nature of the monomer added in the oil phase in step (i).
  • the monomer added in step (i) is chosen in the group consisting of at least one polyisocyanate having at least two isocyanate functional groups; poly maleic anhydride such as Biphenyltetracarboxylic dianydride; poly acyl chloride such as Terepthaloyl chloride or 1,3,5-Benzenetricarbonyl trichloride; polyepoxide such as poly[(o-cresyl glycidyl ether)-co-formaldehyde] ; acrylate monomers such as trimethylolpropane triacrylate and polyalkoxysilane.
  • poly maleic anhydride such as Biphenyltetracarboxylic dianydride
  • poly acyl chloride such as Terepthaloyl chloride or 1,3,5-Benzenetricarbonyl trichloride
  • polyepoxide such as poly[(o-cresyl glycidyl ether)-co-formalde
  • the monomer used in the process according to the invention is present in amounts representing from 0.1 to 15%, preferably from 0.5 to 8% and more preferably from 0.5 to 6% by weight of the microcapsule slurry.
  • the monomer added in step (i) is at least one polyisocyanate having at least two isocyanate functional groups.
  • Suitable polyisocyanates used according to the invention include aromatic polyisocyanate, aliphatic polyisocyanate and mixtures thereof. Said polyisocyanate comprises at least 2, preferably at least 3 but may comprise up to 6, or even only 4, isocyanate functional groups. According to a particular embodiment, a triisocyanate (3 isocyanate functional group) is used.
  • said polyisocyanate is an aromatic polyisocyanate.
  • aromatic polyisocyanate is meant here as encompassing any polyisocyanate comprising an aromatic moiety. Preferably, it comprises a phenyl, a toluyl, a xylyl, a naphthyl or a diphenyl moiety, more preferably a toluyl or a xylyl moiety.
  • Preferred aromatic polyisocyanates are biurets, polyisocyanurates and trimethylol propane adducts of diisocyanates, more preferably comprising one of the above-cited specific aromatic moieties.
  • the aromatic polyisocyanate is a polyisocyanurate of toluene diisocyanate (commercially available from Bayer under the tradename Desmodur ® RC), a trimethylol propane-adduct of toluene diisocyanate (commercially available from Bayer under the tradename Desmodur ® L75), a trimethylol propane-adduct of xylylene diisocyanate (commercially available from Mitsui Chemicals under the tradename Takenate ® D-110N).
  • the aromatic polyisocyanate is a trimethylol propane-adduct of xylylene diisocyanate.
  • said polyisocyanate is an aliphatic polyisocyanate.
  • aliphatic polyisocyanate is defined as a polyisocyanate which does not comprise any aromatic moiety.
  • Preferred aliphatic polyisocyanates are a trimer of hexamethylene diisocyanate, a trimer of isophorone diisocyanate, a trimethylol propane-adduct of hexamethylene diisocyanate (available from Mitsui Chemicals) or a biuret of hexamethylene diisocyanate (commercially available from Bayer under the tradename Desmodur ® N 100), among which a biuret of hexamethylene diisocyanate is even more preferred.
  • the at least one polyisocyanate is in the form of a mixture of at least one aliphatic polyisocyanate and of at least one aromatic polyisocyanate, both comprising at least two or three isocyanate functional groups, such as a mixture of a biuret of hexamethylene diisocyanate with a trimethylol propane-adduct of xylylene diisocyanate, a mixture of a biuret of hexamethylene diisocyanate with a polyisocyanurate of toluene diisocyanate and a mixture of a biuret of hexamethylene diisocyanate with a trimethylol propane-adduct of toluene diisocyanate.
  • the molar ratio between the aliphatic polyisocyanate and the aromatic polyisocyanate is ranging from 80:20 to 10:90.
  • the content of water is below or equal to 10%, preferably below or equal to 5%, more preferably below or equal to 3% by weight based on the total weight of the dispersing phase.
  • the dispersing phase is free of water.
  • step (ii) namely in the dispersing phase.
  • the dispersing phase is hydrophilic.
  • core-shell microcapsules could be obtained by substituting water used in known process from the prior art with solvent(s) preferably chosen in the group consisting of glycerol, 1,4-butanediol, ethylene glycol and mixtures thereof.
  • the solvent used in the dispersing phase is present in amounts representing from 40 to 95%, preferably from 50 to 90% and more preferably from 50 to 80% by weight of the microcapsule slurry.
  • the process of the present invention includes the use of an emulsifier that can be non-ionic and/or ionic in the preparation of the dispersant phase.
  • Suitable ionic emulsifiers include in particular gum Arabic, lignin sulfonate, soy protein, sodium caseinate, gelatin, bovine serum albumin, sugar beet pectin, hydrolyzed soy protein, hydrolyzed sericin, Pseudocollagen, Biopolymer SA-N, Pentacare-NA PF, co-polymers of acrylamide and acrylic acid, acrylic co-polymers bearing a sulfonate group, anionic polyvinyl alcohol, cationic polyvinyl alcohol, and mixtures thereof.
  • Suitable non-ionic emulsifiers are chosen in the group consisting of polyvinylpyrrolidone, polyvinyl alcohol, co-polymers of vinyl ethers and maleic anhydride, modified polyvinyl alcohol, modified starch, modified cellulose, polysaccharides and mixtures thereof.
  • modified it is meant that the modified compound is prepared by physically, enzymatically, or chemically treating the native compound to change its properties.
  • the emulsifier is preferably comprised in an amount ranging from 0.1 to 5.0% by weight of the microcapsule slurry, preferably between 0.5 and 2 wt% of the microcapsule slurry.
  • the dispersing phase may contain a minimum amount of water necessary to dissolve the emulsifier.
  • microcapsules according to the present invention have a shell that is formed by interfacial polymerization.
  • a skilled person in the art is well aware of various ways to induce interfacial polymerization.
  • the dispersing phase comprises nucleophiles groups, preferably with active hydrogen atoms.
  • the dispersing phase comprises a reactant, preferably chosen in the group consisting of a polyamine, a polyol, a polythiol, polyamino alcohol and mixtures thereof.
  • the reactant is a polyamine, preferably chosen in the group consisting of guanidine salts, tris-(2-aminoethyl)amine, N,N,N',N'-tetrakis(3-aminopropyl)-1,4-butanediamine, guanazole, aminoacids such as lysine, aminoalcohol such as 2-amino-1,3-propanediol, ethanolamine and mixtures thereof.
  • guanidine salts tris-(2-aminoethyl)amine, N,N,N',N'-tetrakis(3-aminopropyl)-1,4-butanediamine, guanazole, aminoacids such as lysine, aminoalcohol such as 2-amino-1,3-propanediol, ethanolamine and mixtures thereof.
  • the nature of the shell depends on the nature of the monomer present in the oil phase and the reactant present in the dispersing phase.
  • microcapsules produced in the process according to the present invention are polyurea-based capsules.
  • interfacial polymerization is induced by addition of a polyamine reactant in the dispersing phase to form a polyurea wall with a polyisocyanate present in the oil phase.
  • polyurea-based capsules are formed in absence of added polyamine reactant, and result only from the autopolymerization of the at least one polyisocyanate.
  • microcapsules produced in the process according to the present invention are polyurethane-based capsules.
  • interfacial polymerization is induced by the presence of a polyol in the dispersing phase (that can be the solvent itself, for example glycerol) and/or by the addition of a polyol reactant in the dispersant phase to form a polyurethane wall with a polyisocyanate present in the oil phase.
  • a polyol reactant is selected from the group consisting of monomeric and polymeric polyols with multiple hydroxyl groups available for reaction and mixtures thereof.
  • capsules produced in the process according to the present invention are polyurea/polyurethane based.
  • interfacial polymerization is induced by addition of a mixture of the reactant mentioned under both precedent embodiments.
  • crosslinkers with both amino groups and hydroxyl groups can be used to generate polyurea/polyurethane materials.
  • polyisocyanates with both urea and urethane functionalities can be used to generate polyurea/polyurethane materials.
  • the monomer present in the oil phase is poly maleic anhydride or poly acyl chloride and interfacial polymerization is induced by addition of a polyamine reactant or a polyol reactant (that can be the solvent present in the dispersing phase) leading respectively to polyamide-based microcapsules or polyester-based microcapsules.
  • the monomer present in the oil phase is polyepoxide and interfacial polymerization is induced by addition of a polyamine reactant leading to polyamino-alcohol-based microcapsules.
  • the monomer present in the oil phase is polyurea-polyalkoxysilane copolymer, and interfacial polymerization is induced by the hydrolysis and condensation of the alkoxysilane groups.
  • the dispersing phase comprises an aminoresin.
  • the mean droplet size in the two-phases dispersion is comprised between 1 and 3000 ⁇ m leading to microcapsules having a size comprised between 1 and 3000 ⁇ m.
  • the mean droplet size is comprised between 1 and 500 ⁇ m, preferably between 5 and 50 ⁇ m.
  • microcapsules can be easily adjusted by the skilled person as a function of the nature of the desired application.
  • a polymer selected from the group consisting of a non-ionic polysaccharide, a cationic polymer and mixtures thereof to form an outer coating to the microcapsule.
  • Such coating will help to drive capsule deposition and retention on substrate when applied from rinse-off products so that a significant part of the capsules which have not been broken in the wash phase / upon lathering would transfer to the substrate (skin, hair fabrics) and be available for perfume release when the capsules are broken upon rubbing after drying.
  • Non-ionic polysaccharide polymers are well known to a person skilled in the art.
  • Preferred non-ionic polysaccharides are selected from the group consisting of locust bean gum, xyloglucan, guar gum, hydroxypropyl guar, hydroxypropyl cellulose and hydroxypropyl methyl cellulose.
  • Cationic polymers are also well known to a person skilled in the art.
  • Preferred cationic polymers have cationic charge densities of at least 0.5 meq/g, more preferably at least about 1.5 meq/g, but also preferably less than about 7 meq/g, more preferably less than about 6.2 meq/g.
  • the cationic charge density of the cationic polymers may be determined by the Kjeldahl method as described in the US Pharmacopoeia under chemical tests for Nitrogen determination.
  • the preferred cationic polymers are chosen from those that contain units comprising primary, secondary, tertiary and/or quaternary amine groups that can either form part of the main polymer chain or can be borne by a side substituent directly connected thereto.
  • the weight average (Mw) molecular weight of the cationic polymer is preferably between 10,000 and 3.5M Dalton, more preferably between 50,000 and 2M Dalton.
  • copolymers shall be selected from the group consisting of polyquaternium-5, polyquaternium-6, polyquaternium-7, polyquaternium10, polyquaternium-11, polyquaternium-16, polyquaternium-22, polyquaternium-28, polyquaternium-43, polyquaternium-44, polyquaternium-46, cassia hydroxypropyltrimonium chloride, guar hydroxypropyltrimonium chloride of polygalactomannan 2-hydroxypropyltrimethylammonium chloride ether, starch hydroxypropyltrimonium chloride and cellulose hydroxypropyltrimonium chloride
  • Salcare ® SC60 cationic copolymer of acrylamidopropyltrimonium chloride and acrylamide, origin: BASF
  • Luviquat ® such as the PQ 11N, FC 550 or Style (polyquaternium-11 to 68 of quaternized copolymers of vinylpyrrolidone origin: BASF), or also the Jaguar ® (C13S of C17, origin Solvay ).
  • an amount of polymer described above comprised between about 0% and 5% w/w, or even between about 0.1% and 2% w/w, percentage being expressed on a w/w basis relative to the total weight of the slurry as obtained after step iv). It is clearly understood by a person skilled in the art that only part of said added polymers will be incorporated into/deposited on the microcapsule shell.
  • An object of the invention defines a core-shell microcapsule slurry obtainable by the claimed process; wherein the core shell microcapsules comprise core-shell microcapsules having an oil-based core, wherein the slurry comprises below or equal to 10%, preferably below or equal to 5%, more preferably below or equal to 3% by weight of water based on the total weight of the slurry, and wherein the dispersing phase is hydrophilic.
  • the slurry is free of water.
  • Another object of the invention is a perfuming composition
  • a perfuming composition comprising
  • liquid perfumery carrier one may cite, as non-limiting examples, an emulsifying system, i.e. a solvent and a surfactant system, or a solvent commonly used in perfumery.
  • a solvent and a surfactant system i.e. a solvent and a surfactant system
  • a detailed description of the nature and type of solvents commonly used in perfumery cannot be exhaustive.
  • solvents such as dipropyleneglycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2-ethoxyethoxy)-1-ethanol or ethyl citrate, which are the most commonly used.
  • compositions which comprise both a perfumery carrier and a perfumery co-ingredient can be also ethanol, water/ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar ® (origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark Dowanol ® (origin: Dow Chemical Company).
  • perfumery co-ingredient it is meant here a compound, which is used in a perfuming preparation or a composition to impart a hedonic effect and which is not a microcapsule as defined above.
  • perfuming co-ingredients present in the perfuming composition do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the intended use or application and the desired organoleptic effect.
  • these perfuming co-ingredients belong to chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin.
  • co-ingredients are in any case listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA , or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery. It is also understood that said co-ingredients may also be compounds known to release in a controlled manner various types of perfuming compounds.
  • perfumery adjuvant we mean here an ingredient capable of imparting additional added benefit such as a color, a particular light resistance, chemical stability, etc.
  • additional added benefit such as a color, a particular light resistance, chemical stability, etc.
  • the perfuming composition according to the invention comprises between 0.05 to 30%, preferably between 0.1 and 30 % by weight of microcapsules as defined above.
  • Microcapsules can advantageously be used in many application fields and used in consumer products. Microcapsules can be used in liquid form applicable to liquid consumer products or applicable to solid consumer products.
  • a consumer product preferably in the form of a laundry care product, a home care product, a body care product, a skin care product, a hair care product, an air care product, or a hygiene product, comprising microcapsules as defined above, or a perfuming composition as defined above is also presently disclosed.
  • Another object of the present invention is a liquid consumer product comprising:
  • liquid consumer product comprising:
  • the invention also defines a powder consumer product comprising
  • the consumer product is anhydrous.
  • microcapsules slurry obtained by the process of the invention does not need to be dried before being incorporated in anhydrous consumer product.
  • dispersing phase is compatible with anhydrous consumer product bases.
  • the liquid consumer product comprises less than about 10%, preferably less than about 5%, even preferably less than about 1%, even preferably less than about 0.5% by weight of water based on the total weight of the consumer product.
  • the anhydrous consumer product is free of water.
  • the products of the invention can in particular be of used in perfumed consumer products such as product belonging to fine fragrance or "functional" perfumery.
  • Functional perfumery includes in particular personal-care products including hair-care, body cleansing, skin care, hygiene-care as well as home-care products including laundry care and air care.
  • another object of the present invention consists of a perfumed consumer product comprising as a perfuming ingredient, the microcapsules defined above or a perfuming composition as defined above.
  • the perfume element of said consumer product can be a combination of perfume microcapsules as defined above and free or non-encapsulated perfume, as well as other types of perfume microcapsule than those here-disclosed.
  • microcapsules can therefore be added as such or as part of an invention's perfuming composition in a perfumed consumer product.
  • perfumed consumer product it is meant a consumer product which is expected to deliver among different benefits a perfuming effect to the surface to which it is applied (e.g. skin, hair, textile, paper, or home surface) or in the air (air-freshener, deodorizer etc).
  • a perfumed consumer product according to the invention is a manufactured product which comprises a functional formulation also referred to as "base”, together with benefit agents, among which an effective amount of microcapsules produced in the process according to the invention.
  • Non-limiting examples of suitable perfumery consumer product can be a perfume, such as a fine perfume, a cologne or an after-shave lotion; a fabric care product, such as a liquid or solid detergent, tablets and pods, a fabric softener, a dryer sheet, a fabric refresher, an ironing water, or a bleach; a body-care product, such as a hair care product (e.g. a shampoo, hair conditioner, a colouring preparation or a hair spray), a cosmetic preparation (e.g. a vanishing cream, body lotion or a deodorant or antiperspirant), or a skin-care product (e.g.
  • a hair care product e.g. a shampoo, hair conditioner, a colouring preparation or a hair spray
  • a cosmetic preparation e.g. a vanishing cream, body lotion or a deodorant or antiperspirant
  • a skin-care product e.g.
  • a perfumed soap, shower or bath mousse, body wash, oil or gel, bath salts, or a hygiene product a perfumed soap, shower or bath mousse, body wash, oil or gel, bath salts, or a hygiene product
  • an air care product such as an air freshener or a "ready to use” powdered air freshener
  • a home care product such all-purpose cleaners, liquid or tablet dishwashing products, toilet cleaners or products for cleaning various surfaces, for example sprays & wipes intended for the treatment / refreshment of textiles or hard surfaces (floors, tiles, stone-floors etc.), a hygiene product such as sanitary napkins, diapers, toilet paper.
  • the consumer product is selected from the group consisting of a shampoo, a shower gel, a rinse-off conditioner, a soap bar, or a liquid detergent, a fabric softener and a floor cleaner.
  • the consumer product is a shampoo or a rinse-off conditioner.
  • the product is a perfumed soap.
  • the product is a body wash.
  • the product is a fabric care product.
  • Another object of the disclosure is a powder detergent comprising:
  • Powder detergent active base in which the microcapsules can be incorporated can be found in the abundant literature relative to such products. These formulations do not warrant a detailed description here which would in any case not be exhaustive. The person skilled in the art of formulating such consumer products is perfectly able to select the suitable components on the basis of his general knowledge and of the available literature.
  • liquid detergent consumer product there are the individual liquid detergent pods having almost an anhydrous composition.
  • the inclusion level of standard microcapsules in this very specific format is limited due the presence of water in the slurry as it can easily dissolve the film (typically PvOH).
  • microcapsules obtained by the process of the invention increases the amount of capsules within the formulation without compromising the film properties.
  • Another object of the invention is a liquid detergent pod comprising:
  • the pod generally consists of a film made of PVOH.
  • Liquid detergent active base in which the microcapsules can be incorporated can be found in the abundant literature relative to such products. These formulations do not warrant a detailed description here which would in any case not be exhaustive. The person skilled in the art of formulating such consumer products is perfectly able to select the suitable components on the basis of his general knowledge and of the available literature.
  • a solid scent booster composition comprising:
  • the solid scent booster composition is in a pastillized form.
  • the microcapsules slurry is mixed with the carrier in a molten state to obtain a homogeneous mixture. Then, the mixture can be poured drop wise on a support to obtain solidified pastilles.
  • Any material that can be easily molten and solidified can be used a carrier in the present invention.
  • the carrier is chosen in the group consisting of PEG, fatty alcohols and mixtures thereof.
  • PEG has preferably a molecular weight greater than 1000g/mol, preferably between 1000 and 8000g/mol.
  • Fatty alcohols have preferably 20 or more carbon atoms.
  • the consumer products as defined above comprises from 0.05 wt%, preferably from 0.1 to 15wt%, more preferably between 0.2 and 5wt%, even more preferably between 1 and 5% of the microcapsules of the present invention, these percentages being defined by weight relative to the total weight of the consumer product.
  • concentrations may be adapted according to the olfactive effect desired in each product.
  • glycerol (Origin: Alfa Aesar) containing 3% (w/w) of casein sodium salt (Origin:Sigma Aldrich) were introduced into a reactor and heated to 70°C.
  • the oil phase containing 30 g of perfume A (see table 1) and 0.6 g of a polyisocyanate (trimethylol propane adduct of xylylene diisocyanate, Takenate ® D-110N, origin: Mitsui Chemicals) was added in the glycerol phase then mechanically stirred at 800RTM during 5 min to obtain an emulsion.
  • the emulsion was kept at 300 RPM for 7 hours at 70°C.
  • glycerol phase containing 3% (w/w) of casein sodium salt (Origin: Sigma Aldrich) were introduced in a reactor and heated to 70°C.
  • the oil phase prepared by mixing 0.6g of a polyisocyanate (trimethylol propane adduct of xylylene diisocyanate, Takenate ® D-110N, origin: Mitsui Chemicals) and 30g of perfume A (see table 1), was added in the glycerol phase.
  • the emulsion was obtained by using an anchor rotor at 800 RPM during 5 minutes and kept at 70°C.
  • guanidine carbonate (Origin: Alfa Aesar) were dissolved in 8.8 g of glycerol and added to the emulsion.
  • the emulsion was kept at 300 RPM for 7 hours at 70°C. The stirring was then stopped and the system was cooled down at room temperature. The average size of the resulting microcapsules was close to 15 ⁇ m.
  • Microcapsules prepared in examples 1 and 2 were washed 3 times with water to remove glycerol and analyzed with Thermogravimetric analyzer (TGA, Mettler-Toledo, Switzerland) to assess their perfume retention.
  • the microcapsules sample (10 to 20 mg) was introduced into an aluminium oxide crucible and its remaining mass was determined by TGA under controlled temperature and a constant flow of nitrogen of 20 mL/min.
  • the sample was heated from 25°C to 50°C at a rate of 10 °C/min then the temperature was kept constant for about two hours. Results are shown in Figure 1 . In both cases, the isotherm curves present a plateau which indicates good perfume retention.
  • glycerol phase containing 1% (w/w) of polyvinylpyrolidone (Origin: sigma Aldrich) and 1% (w/w) of poly(1-vinylpyrrolidone co-vinyl acetate) (Origin:Sigma Aldrich) were introduced in a reactor and heated to 50°C.
  • the oil phase prepared by dissolving at 50°C 2g of a polyisocyanate (trimethylol propane adduct of xylylene diisocyanate, Takenate ® D-110N, origin: Mitsui Chemicals) and 30g of perfume A (see table 1) was added to the glycerol phase.
  • the emulsion was obtained by stirring this mixture with an anchor rotor at 600RPM during 3 minutes at 50°C. 0.28g of 1,2-diaminocyclohexane (Origin:Sigma Aldrich) mixed with 7.7g of glycerol were added to the emulsion that was then kept at 300 RPM for 5 hours at 50°C. At the end of the polymerization process, the stirring was stopped and the system was cooled down at room temperature. The average size of the resulting microcapsules was closed to 10 ⁇ m (see figures 2a and 2b).
  • Capsules A5 60g of glycerol phase containing 3% (w/w) of casein sodium were introduced into a reactor and heated to 70°C.
  • the oil phase was prepared by dissolving 0.6g poly[(o-cresyl glycidyl ether)-co-formaldehyde] (Origin:sigma Aldrich) in 30g of perfume A (see table 1), was added in the glycerol phase.
  • the emulsification was obtained by shearing with the anchor rotor at 600RPM during 3 min at 70°C.
  • Capsules B5 Solution (60 g) of casein sodium (3 wt%) in glycerol was placed into a reactor.
  • the oil phase composed of trimethylol triglycidyl ether (2.02 g, Sigma Aldrich) and perfume B (30 g), was added dropwise at room temperature to the glycerol phase.
  • the resulting mixture was stirred at 600 RPM with an anchor rotor during 2 minutes at 50°C to obtain an emulsion.
  • a solution of 1,2-diaminocyclohexane (1.14 g, Sigma Aldrich) in glycerol (5 g) was added over the course of one hour.
  • Capsules C5 Solution (60 g) of casein (3 wt%) in glycerol was placed into a reactor.
  • the oil phase composed of poly[(o-cresyl glycidyl ether)-co-formaldehyde] (1.20 g, Sigma Aldrich) and perfume B (30 g), was added dropwise at room temperature to the glycerol phase.
  • the resulting mixture was stirred at 600 rpm with an anchor rotor during 2 minutes at 50°C to obtain an emulsion.
  • a solution of tris-2-aminoethylamine (2.70 g, Sigma Aldrich) in glycerol (2 g) was added over the course of one hour.
  • the reaction mixture was kept under stirring at 600 rpm during one hour at 50°C.
  • a solution of DABCO (0.05 g) in glycerol (2.5 g) was added and the reaction mixture was warmed at 80°C for two hours.
  • Capsules D5 Solution (60 g) of casein (3 wt%) in glycerol was placed into a reactor.
  • the oil phase composed of poly[(o-cresyl glycidyl ether)-co-formaldehyde] (1.20 g, Sigma Aldrich) and perfume B (30 g), was added dropwise at room temperature to the glycerol phase.
  • the resulting mixture was stirred at 600 rpm with an anchor rotor during 2 minutes at 50°C to obtain an emulsion.
  • 2-ethanolamine (2.70 g, Sigma Aldrich) in glycerol (2 g) was added over the course of one hour.
  • the reaction mixture was kept under stirring at 600 rpm during one hour at 50°C.
  • a solution of DABCO (0.05 g) in glycerol (2.5 g) was added and the reaction mixture was warmed at 80°C for two hours.
  • glycerol contain 1% (w/w) of Superstab Gum Arabic (from Nexira), 1%(w/w) of acid lignosulfonic sodium salt (Sigma Aldrich) and 5% (w/w) of di-ionized water were placed in a reactor and maintained at 50°C.
  • the oil phase was heated to 50°C and added in the glycerol phase.
  • the emulsification was achieved by stirring with an anchor rotor at 600RPM during 3 minutes at 50°C.
  • the emulsion's temperature was increased to 75°C and 10 g of 10% HCl solution were added during one hour.
  • the emulsion was kept under mechanical agitation for 5hours at 75°C.
  • Table 3 Composition of perfume C Raw Material % in oil Ethyl 2-methyl-pentanoate 4.00 2,4-Dimethyl-3-cyclohexene-1-carbaldehyde 4.00 Allyl Heptanoate 6.60 (Z)-3-hexen-1-ol Butyrate 1.30 Allyl amyl glycolate 13.10 Delta Damascone 2.00 Verdyl acetate 24.30 Methylnaphtylcetone 1.30 Hedione ®1) 6.60 Iso E Super ® 2) 19.70 Ald.
  • Perfume D was prepared by admixing at equal mass 5 perfumery ingredients: Hexyl salicylate, Romascone ® 1) , Cyclosal 2) , Vertenex ® 3) , and Verdox ® 4) .
  • glycerol solution containing 1% (w/w) of polyvinylalcohol Mowiol 18-88 (Sigma Aldrich) and 5% (w/w) of di-ionized water were placed into a reactor and heated to 50°C.
  • the oil phase prepared by dissolving at room temperature 2g of a polyisocyanate (trimethylol propane adduct of xylylene diisocyanate, Takenate ® D-110N, origin: Mitsui Chemicals), 30g of perfume D, was added to the glycerol phase. The resulting mixture was stirred at 600RPM for 3 min to obtain an emulsion.
  • a polyisocyanate trimethylol propane adduct of xylylene diisocyanate, Takenate ® D-110N, origin: Mitsui Chemicals
  • the stirring rate was decreased to 300RPM while the temperature of the emulsion was increased to 70°C. 0.23g of Guanidine Carbonate, dissolved in 7.85g of glycerol, was added into the reactor and the reaction mixture was kept under stirring for 7 hours at 70°C. The average size of the obtained microcapsules was close to 15 ⁇ m.
  • terephtaloyl chloride (1.29 g, origin: Aldrich) and perfume D (19.93 g, origin: Firmenich SA) were mixed under magnetic stirring for 15 min to afford an oil phase.
  • the oil phase was added dropwise to the glycerol phase under vigorous mechanical stirring to afford an emulsion.
  • the reaction mixture was stirred at RT until the formation of microcapsules.
  • Microcapsules prepared in example 8 were introduced in a shower gel base (see table 4) in such way to obtained 0.5% of perfume content.
  • the sample was kept at room temperature and the stability of the microcapsules was assessed at different time by quantifying the free perfume in the base.
  • the result depicted in Figure 4 shows good storage stability of the microcapsules in shower gel base.
  • Fabric softener base formulation comprising microcapsules prepared by the process of the invention
  • Microcapsule D5 prepared in example 5 (0.19 g) are introduced in a fabric softener base (49.8 g, see table 5) in such way to obtained 0.11% of perfume content.
  • Table 5 Fabric softener base composition Ingredients Quantity (%) Water 90.72 Stepantex VL 90A 8.88 Calcium chloride solution at 10% 0.36 Proxel GXL 0.04
  • Powder detergent formulation comprising microcapsules prepared by the process of the invention
  • microcapsules obtained in Example 8 are incorporated in a commercially available powder detergent (Persil Universal, origin: Henkel, Germany) at a inclusion level of respectively 1% and 1.5%
  • Powder detergent formulation sodium percarbonate, benzenesulfonic acid, C10-13-alkyl derivs sodium salts, sodium carbonate, sulfuric acid, mono C12-18 alkyl esters sodium salts, alcohols ethoxylated.
  • Liquid detergent dose formulation comprising microcapsules prepared by the process of the invention
  • Example 8 Incorporation of microcapsules obtained in Example 8 are introduced at the rate of 1.5% and 3% slurry in a commercially available standard unit dose liquid detergent base with single compartment from Unilever called Persil Small & Mighty Bio Capsules, origin: Unilever, UK), packaged in PVOH sachets.
  • Persil small & mighty bio capsules formulation mea-dodecylbenzesulfonate, mea-hydrogenated cocoate, propylene glycol, c12-15 pareth-7, aqua, glycerin, polyvinyl alcohol, perfume, pentasodium ethylenediamine tetramethylene phosphonate, ethanolamine, sorbitol, mea-sulfate, pvp, subtilisin, glycol, butylphenyl methypropional, starch, hexal cinaamal, boronic acid, (4,formylphenal), limonene, lianlool, dosodium distyrylbiphenyl disulfonate, alpha-isomethyl ionone, talc, amylase, polymeric blue colourant, sodium chloride, mannamase, polymeric yellow colourant.
  • Ariel pods capsules formulation mea-dodecylbenzenesulfonate, propylene glycol, c12-14 pareth-7, mea-laureth sulfate, aqua, pei ethoxylate, glycerin, perfume, co-polymer of peg / vinyl acetate, dodecylbenzene sulfonic acid, potassium sulfite, magnesium chloride, peg/ppg-10/2 propylheptyl ether, benzyl salicylate, hydrogenated castor oil, ethanolamine, polystyrene, hexyl cinnamal, citronellol, butylphenyl methylpropional, sodium formate, sorbitol, protease, linalool, coumarin, tripropylene glycol, 2-propcnoic acid, polymer with ethenylbenzene, disodium distyrylbiphenyl disulfonate, gerani
  • Polyethylene glycol based solid scent booster comprising microcapsules prepared by the process of the invention
  • PEG 4000 Polyethyleneglycol (PEG) 4000 are heated to obtain a water clear liquid.
  • 0.9g of microcapsule slurry prepared in example 8 are added to the molten PEG and the mixture is shortly agitated by means of a magnetic stir bar to obtain a homogenous mixture.
  • the liquid capsule dispersion is then poured drop wise (to obtain pastilles) or in a slow, continuous and strand like manner onto a stainless steel plate. After solidification the PEG pastilles are collected. In the case of strands the PEG material is broken into small pieces and finally also applied as solid scent booster in wash applications.

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Claims (14)

  1. Procédé de préparation d'une suspension de microcapsules, le procédé comprenantà :
    (i) la dissolution d'un monomère dans une phase huileuse comprenant un ingrédient hydrophobe actif, de préférence un parfum ;
    (ii) la préparation d'une phase de dispersion comprenant un émulsifiant, dans lequel la phase de dispersion n'est pas miscible avec la phase huileuse ;
    (iii) l'ajout de la phase huileuse à la phase de dispersion pour former une dispersion à deux phases ;
    (iv) l'application des conditions suffisantes pour induire une polymérisation interfaciale et former des microcapsules noyau-enveloppe sous forme d'une suspension ;
    dans lequel le monomère est susceptible de réagir durant la polymérisation interfaciale pour former les microcapsules sous forme d'une suspension ;
    ledit procédé étant caractérisé en ce que la teneur en eau dans la phase de dispersion est inférieure ou égale à 10 % en poids sur la base du poids total de la phase de dispersion, et caractérisé en ce que la phase de dispersion est hydrophile.
  2. Procédé selon la revendication 1, dans lequel la teneur en eau dans la phase de dispersion est inférieure ou égale à 5 % en poids sur la base du poids total de la phase de dispersion.
  3. Procédé selon la revendication 1 ou 2, dans lequel la phase de dispersion ne comprend pas d'eau.
  4. Procédé selon l'une quelconque des revendications précédentes, dans lequel la phase de dispersion comprend des groupes de nucléophiles.
  5. Procédé selon l'une quelconque des revendications précédentes, dans lequel la phase de dispersion comprend un solvant choisi dans le groupe constitué de glycérol, 1,4-butanediol, éthylène glycol et des mélanges de ceux-ci.
  6. Procédé selon l'une quelconque des revendications précédentes, dans lequel le monomère dans la phase huileuse est choisi dans le groupe constitué d'au moins un polyisocyanate, polyanhydride maléique, polychlorure d'acyle, polyépoxyde, monomères d'acrylate et polyalcoxysilane.
  7. Procédé selon l'une quelconque des revendications précédentes, dans lequel la phase de dispersion comprend une polyamine, choisie de préférence dans le groupe constitué de sels de guanidine, tris-(2-aminoéthyl)amine, N,N,N',N'-tétrakis(3-aminopropyl)-1,4-butanediamine, guanazole, acides aminés tels que lysine, alcool aminé tel que 2-amino-1,3-propanediol, éthanolamine et des mélanges de ceux-ci.
  8. Procédé selon l'une quelconque des revendications précédentes, dans lequel la phase de dispersion comprend un polyol.
  9. Procédé selon l'une quelconque des revendications précédentes, dans lequel l'émulsifiant est choisi dans le groupe constitué de gomme arabique, sulfonate de lignine, protéine de soja, caséinate de sodium, gélatine, sérum-albumine bovine, pectine de betterave à sucre, protéine de soja hydrolysée, séricine hydrolysée, collagène végétal, biopolymère SA-N, Pentacare-NA PF, copolymères d'acrylamide et d'acide acrylique, copolymères acryliques portant un groupe sulfonate, alcool de polyvinyle anionique, alcool de polyvinyle cationique, polyvinylpyrrolidone, alcool de polyvinyle, copolymères d'éthers de vinyle et d'anhydride maléique, alcool de polyvinyle modifié, amidon modifié, cellulose modifiée, polysaccharides et des mélanges de ceux-ci.
  10. Suspension de microcapsules noyau-enveloppe pouvant être obtenue par le procédé comme définie dans une quelconque des revendications 1-9 ; où la suspension comprend moins de ou égal éà 10 %, de préférence moins de ou égal à 5 %, plus préférentiellement moins de ou égal à 3 % en poids d'eau sur la base du poids total de la suspension, et où la phase de dispersion est hydrophile.
  11. Composition parfumante comprenant :
    (i) une suspension de microcapsules comme définie dans la revendication 10, dans laquelle l'ingrédient hydrophobe actif comprend un parfum ;
    (ii) au moins un ingrédient sélectionné parmi le groupe constitué d'un support de parfumerie et d'un co-ingrédient parfumant ; et
    (iii) optionnellement un adjuvant d'usage courant en parfumerie.
  12. Produit de consommation liquide, de préférence sous forme d'un produit de soin du linge, d'un produit de soins domestiques, d'un produit de soins pour le corps, d'un produit de soins pour la peau, d'un produit assainisseur d'air ou d'un produit d'hygiène, ledit produit de consommation comprenant :
    a) de 2 à 65 % en poids, par rapport au poids total du produit de consommation, d'au moins un tensioactif ;
    b) de l'eau ou un solvant organique hydrophile miscible avec de l'eau ; et
    c) une suspension de microcapsules comme définie dans la revendication 10 ou une composition parfumante comme définie dans la revendication 11,
    où ledit produit de consommation liquide comprend moins de 10 % en poids d'eau sur la base du poids total du produit de consommation.
  13. Produit de consommation en poudre comprenant
    a) de 2 à 65 % en poids, par rapport au poids total du produit de consommation, d'au moins un tensioactif ; et
    b) une composition parfumante comme définie dans la revendication 11 ou une suspension de microcapsules comme définie dans la revendication 10.
  14. Produit de consommation selon la revendication 13 sous forme d'un produit de consommation anhydre, dans lequel le produit de consommation comprend moins de 10 % en poids d'eau sur la base du poids total du produit de consommation.
EP18732389.4A 2017-06-27 2018-06-27 Procédé de préparation d'une barbotine de microcapsules Active EP3645157B1 (fr)

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EP17178019 2017-06-27
PCT/EP2018/067273 WO2019002380A1 (fr) 2017-06-27 2018-06-27 Processus pour la préparation de microcapsules

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EP3645157B1 true EP3645157B1 (fr) 2023-09-27

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EP (1) EP3645157B1 (fr)
JP (1) JP7346306B2 (fr)
CN (1) CN110785227A (fr)
MX (1) MX2019013232A (fr)
SG (1) SG11201909150XA (fr)
WO (1) WO2019002380A1 (fr)

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SG11202105921RA (en) * 2018-12-19 2021-07-29 Firmenich & Cie Process for preparing polyamide microcapsules
JP7395612B2 (ja) 2019-04-17 2023-12-11 ザ プロクター アンド ギャンブル カンパニー カプセル
WO2020214878A1 (fr) 2019-04-17 2020-10-22 The Procter & Gamble Company Procédés de fabrication de capsules
MX2021012434A (es) 2019-04-17 2022-01-19 Procter & Gamble Capsulas.
WO2020231351A2 (fr) * 2019-04-24 2020-11-19 Chulalongkorn University Procédé de préparation d'une émulsion d'huile essentielle
EP3969166A1 (fr) 2019-05-16 2022-03-23 Gem Innov Procede de preparation de microcapsules biodegradables et microcapsules ainsi obtenues
WO2020234263A1 (fr) * 2019-05-21 2020-11-26 Firmenich Sa Microcapsules de poly(ester-urée)
US20220072498A1 (en) * 2019-05-21 2022-03-10 FlRMENICH SA Process for preparing microcapsules
EP3921075B1 (fr) * 2019-08-05 2024-06-12 Firmenich SA Microcapsules clivables à base de plusieurs alcools
EP3921076A1 (fr) * 2019-08-05 2021-12-15 Firmenich SA Microcapsules de poly(amide-ester)
CN111363522B (zh) * 2020-04-01 2021-06-01 迈科凯普(杭州)生物科技有限公司 一种应用在织物的多层蓄热保温微胶囊及制备方法
US11938349B2 (en) 2020-10-16 2024-03-26 The Procter & Gamble Company Antiperspirant and deodorant compositions comprising capsules
WO2022082188A2 (fr) 2020-10-16 2022-04-21 The Procter & Gamble Company Compositions liquides pour l'entretien des tissus comprenant des capsules
US12077728B2 (en) 2020-10-16 2024-09-03 The Procter & Gamble Company Laundry care additive particles
MX2023004230A (es) 2020-10-16 2023-04-21 Procter & Gamble Articulo de dosis unitaria soluble en agua que contiene una capsula de nucleo/cubierta.
US20220118417A1 (en) * 2020-10-16 2022-04-21 The Procter & Gamble Company Capsules
WO2022092355A1 (fr) * 2020-10-29 2022-05-05 주식회사 인실리코 Microcapsule ayant une structure coeur-écorce et son procédé de production
MX2023002141A (es) * 2020-12-21 2023-03-16 Firmenich & Cie Proceso de preparacion de microcapsulas de poliester.
EP4196257A1 (fr) * 2020-12-21 2023-06-21 Firmenich SA Procédé de préparation de microcapsules de polyester
US20240157322A1 (en) * 2021-03-30 2024-05-16 Firmenich Sa Crosslinked core-shell microcapsules
US20240261750A1 (en) * 2021-06-28 2024-08-08 Firmenich Sa Polyamide-based microcapsules
MX2024000512A (es) * 2021-07-28 2024-01-31 Firmenich & Cie Microcapsulas a base de poliamida.
EP4154974A1 (fr) * 2021-09-23 2023-03-29 International Flavors & Fragrances Inc. Microcapsules biodégradables
CN114130320B (zh) * 2021-10-24 2024-04-16 武汉中科先进材料科技有限公司 电子墨水微胶囊、电子墨水及制备方法和柔性显示屏
WO2024038046A1 (fr) * 2022-08-18 2024-02-22 Basf Se Procédé de production de microparticules

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EP3645157A1 (fr) 2020-05-06
MX2019013232A (es) 2020-01-30
WO2019002380A1 (fr) 2019-01-03
CN110785227A (zh) 2020-02-11
SG11201909150XA (en) 2020-01-30
JP2020525403A (ja) 2020-08-27
US11291969B2 (en) 2022-04-05
JP7346306B2 (ja) 2023-09-19
US20200129947A1 (en) 2020-04-30

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